Related Experiment Video
Updated: Jan 3, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Inserting Nitrogen: An Effective Concept To Create Nonplanar and Stimuli-Responsive Perylene Bisimide Analogues
Sakiho Hayakawa1, Ayumi Kawasaki2,3, Yongseok Hong4
1Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering , Nagoya University , Furo-cho, Chikusa-ku , Nagoya , Aichi 464-8603 , Japan.
Researchers developed novel nonplanar molecules called dinaphtho[1,8-bc:1
Area of Science:
- Materials Science
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Developing nonplanar π-conjugated molecules is essential for advanced functional materials.
- Perylene bisimide (PBI) derivatives are widely studied for their electronic properties.
Purpose of the Study:
- To synthesize and characterize novel dinaphtho[1,8-bc:1',8'-ef]azepine bisimides (DNABIs).
- To investigate the structure-property relationships of DNABIs based on their nonplanar conformations.
Main Methods:
- Synthesis of various DNABI derivatives with different substituents on the central nitrogen atom.
- Structural analysis using techniques sensitive to conformation and electronic properties.
- Investigation of redox activity and response to external stimuli.
Main Results:
- Synthesized DNABIs exhibit nonplanar structures with flexible conformations (bent and twisted).
- Steric effects around the nitrogen atom dictate molecular conformation and electronic properties.
- Nonsymmetric DNABIs show unique electric-field-induced structural changes.
- Chiral induction in N-unsubstituted DNABIs achieved through hydrogen bonding.
Conclusions:
- DNABIs represent a new class of nonplanar π-conjugated molecules with tunable properties.
- Conformational flexibility and steric control are key design principles for functional materials.
- DNABIs demonstrate potential for applications in responsive materials and chiral technologies.
More Related Videos
12:51A 'Plug and Play' Method to Create Water-dispersible Nanoassemblies Containing an Amphiphilic Polymer, Organic Dyes and Upconverting Nanoparticles
Published on: November 14, 2015
09:34Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Related Concept Videos
Diazonium Group Substitution: –OH and –H
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Preparation of Nitriles
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Pericyclic Reactions: Introduction
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...